Holiday home rentals near Chesapeake Bay

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Top-rated holiday home rentals near Chesapeake Bay

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
The exterior of a blue, single-story home is presented, featuring a welcoming front porch with white railings. The front yard is landscaped with shrubs and flowers. A charcoal grill is positioned on the right, and ample parking space is visible in the driveway.
Holiday home in Frankford
4.89 out of 5 average rating, 72 reviews

Charming Beach/Bay Escape with Activities for All!

There's much to do from our comfortable and clean Ocean View vacation home! The beautiful Delaware beaches are a given (10 minute drive to Bethany depending on traffic.) But within a short drive there's fishing, crabbing, hiking, kayaking, golf, putt-putt and more. Just minutes to shopping, antiquing, outlet malls, and superb restaurants. Home amenities as well: large yard, game room, hammock and swings, grill, etc. The very low traffic, private road loops offer safe jogging and biking. Enjoy!

Guest favourite
A welcoming home features large windows overlooking a glistening pool, which invites relaxation. Several lounge chairs are positioned around the pool area, and an umbrella provides shade. The wooden deck extends from the house, enhancing the outdoor space.
Holiday home in Burgess
4.89 out of 5 average rating, 18 reviews

Northern Neck Waterfront

Relax with the whole family at this peaceful waterfront retreat. Nestled along Coles Creek and the Great Wicomico River, this 3-bedroom house is a perfect waterfront getaway with all the amenities you need for a comfortable stay. Savor the beauty of nature from our backyard, where a glistening pool takes center stage, inviting you to unwind and bask in the sun. If you're an aquatic enthusiast or simply someone in search of serenity, our house in Burgess offers an idyllic haven to vacation.

Top guest favourite
The open living area features a cozy seating arrangement with a plush sofa and armchairs, complemented by a rustic wooden dining table that seats six. A flat-screen television is mounted on the wall, and a decorative plant adds a touch of greenery.
Holiday home in Washington
4.99 out of 5 average rating, 108 reviews

Designer apt with high end finishes and furnishing

Located in a large, historic townhouse in the Historic District near Lincoln Park and the Eastern Market this professionally decorated English basement apartment includes original artwork; designer furnishings chosen for comfort; and an open concept living/dining/kitchen accented by a rustic antique dining table that seats up to 6. Lush front garden with cafe' table and seating for 6. The new bathroom features double sinks, lighted medicine cabinets and an extra-large shower. Parking permit..

Guest favourite
Holiday home in Fredericksburg
4.9 out of 5 average rating, 87 reviews

Cheerful 3 bedroom home with sauna

Tucked next to the Frederal civil war park in very quiet 2 acres land at a dead end street but very close to the historic Fredericksburg downtown (In 2026 summer, the pool is closed). You can take 5 minutes short walk to access the civil war park and enjoying more than 10 miles of historical beautiful federal civil war park land. Or you can just stay in the house and relax with the tranquility or the sauna. Or visit the historical Fredericksburg downtown or George Washington boyhood home.

Top guest favourite
The exterior features a welcoming front porch, accessed by brick steps. Two mint green doors lead to separate entrances, with elegant lanterns providing ambient light. A white railing frames the porch, complemented by dark mulch and neatly planted greenery, creating an inviting approach.
Holiday home in Cape Charles
4.98 out of 5 average rating, 45 reviews

Parkside South, Cape Charles

Parkside offers the perfect getaway for families and/or friends! Conveniently located next to Central Park, 2 blocks from the beach and the main street (Mason Ave). In peak summer we have full weeks available (Sun-Sun) or partial (Sun-Thurs). We open corresponding weekends once the Sun-Thurs books. Check our calendar or social media for weekend openings! We recommend a max of 4 adults or 2 adults and 3 (possibly 4) children, depending on their ages. Our family of 5 stays comfortably!

Top guest favourite
A comfortable living area boasts a gray sofa adorned with bright yellow decorative pillows. A wooden coffee table rests in front of the sofa, complemented by an antique trunk nearby. The warm yellow walls are accented with artwork and natural wood doors, creating a welcoming environment.
Holiday home in Milton
5 out of 5 average rating, 49 reviews

Serene Cozy Couples Getaway

Forget your worries in this lovely private getaway that's close to numerous attractions: The upstairs apartment is comfortable with all the amenities needed to make your stay relaxing and enjoyable. We're close to beaches, dining, shopping, and outdoor activities. The charming deck is the perfect spot to relax and enjoy reading a book, having breakfast, dinner, or a nice evening drink. Not suitable for children, pets, Not handicap accessible. No one under 20. No Smoking on premises.

Top guest favourite
A compact in-law suite is displayed, featuring a full kitchen with stainless steel appliances. A comfortable pull-out couch sits adjacent to a wooden coffee table on a patterned rug. A small dining table with two chairs is present, along with a stacked washer and dryer.
Holiday home in Washington
4.96 out of 5 average rating, 292 reviews

In-Law Suite in Van Ness/Cleveland Prk/free parkin

Bright new in-law suite with a separate entrance, full kitchen, washer & dryer, fast internet, pull-out couch, laptop desks, and a pack n' play for little ones. Easy access to National Mall via Van Ness metro stop four minutes away. Flexible check in and check out, no cleaning fees (though smoking, marijuana and incense are a firm no). We've been hosting people from all over the world for several years, and we're happy to help you have a great time in Washington, for leisure or work!

Top guest favourite
Holiday home in Severna Park
5 out of 5 average rating, 49 reviews

Waterfront 5 Bedroom Home Close to Annapolis

Beautiful waterfront 5 bedroom home located off of the Magothy River. Close proximity to many shops & restaurants, downtown Annapolis, the Naval Academy & a short drive from BWI. This home was recently renovated and offers a lot of room to host a weekend away with your family or friends. Enjoy the beautiful sunsets from the private pier and almost 1 acre of land. Feel free to use the kayaks, canoes, & stand up paddleboards to explore the breathtaking views of the Magothy River!

Superhost
A vibrant sunset casts a warm glow over the water, with rich hues of orange, pink, and purple reflected in the calm surface. A dock extends into the scene, framed by grassy edges, contributing to the serene atmosphere along the river.
Holiday home in Gloucester County
4.82 out of 5 average rating, 60 reviews

Waterfront 4 bedroom home with marina facilities

Stunning river views from this spacious family home. The quiet, peaceful setting is perfect for taking in nature and wildlife. The open floor plan that spills onto the patio is great for entertaining. Wonderful spot to enjoy boating, crabbing, fishing, kayaking - all the Severn River has to offer. Home features first floor BR and BR w/ shower, upstairs 3 BR and 2 full BR. Award-Winning Busch Gardens, Historic Colonial Triangle (Yorktown / Williamsburg / Jamestown) Nearby.

Top guest favourite
The exterior of a two-story garage apartment is shown, featuring beige siding and contrasting dark shutters. A distinctive teal sign is mounted above the entrance, while two white garage doors are visible at the base. A tree with green leaves is partially displayed on the right.
Holiday home in Ocean City
4.98 out of 5 average rating, 55 reviews

Vacay Stay-2BR/1Bath, Family Groups Only

Family friendly upstairs, garage apartment. Located on the same property as Dolores by the Sea, only 0.2 miles away from beach and boardwalk. Nestled in a quiet part of town but close to everything. This quaint apartment is perfect for small family’s looking for a relaxing beach vacation. Due to neighborhood restrictions we can only rent to family groups or individuals 25 y/o and over. This is a upstairs unit and may not be for those who have mobility restrictions.

Guest favourite
Holiday home in Heathsville
4.98 out of 5 average rating, 96 reviews

Beachfront Getaway on the Chesapeake Bay!

Recharge, reconnect, and reset by staying at our waterfront home. Spend time with your crew while relaxing in this beautiful, well appointed home featuring stunning wide water views of the Chesapeake Bay. "Almost Heaven" is located at the end of a gravel lane, amongst trees, making it the perfect getaway. The expansive patio and beachfront yard offer infinity views of your private beach. Grab a glass, take a sip and put your toes in the sand!

Superhost
A comfortable bedroom features a spacious bed with floral bedding, complemented by three framed botanical prints on the wall. A cozy chair is positioned next to the bed, and a light rug creates a soft contrast against the wood-like flooring.
Holiday home in Rockville
4.96 out of 5 average rating, 112 reviews

One Bedroom Guest Studio Suite

Come stay at our newly renovated guest suite in the heart of Rockville, MD. The 1-bedroom studio suite is fully furnished with a fully equipped kitchenette and bathroom. Our suite is steps away from public transportation (Route 48) which takes you to the red-line metro (Wheaton or Rockville), and a walkable distance from a shopping center featuring a grocery store, restaurants, etc. There is ample space for parking in front of the property.

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